Dimethylamine → (R)-1-(2-(2-Cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)-N,N-dimethylpiperidine-3-carboxamide

HRID 931200ノート

反応式

HRID 931200 の反応式
[CH3:1][NH:2][CH3:3].C(N(CC)CC)C.[CH:11]1([C:14]2[N:19]=[C:18]([C:20]3[NH:37][C:23]4=[N:24][C:25]([N:28]5[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34](O)=[O:35])[CH2:29]5)=[CH:26][CH:27]=[C:22]4[N:21]=3)[CH:17]=[CH:16][N:15]=2)[CH2:13][CH2:12]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH:11]1([C:14]2[N:19]=[C:18]([C:20]3[NH:37][C:23]4=[N:24][C:25]([N:28]5[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34]([N:2]([CH3:3])[CH3:1])=[O:35])[CH2:29]5)=[CH:26][CH:27]=[C:22]4[N:21]=3)[CH:17]=[CH:16][N:15]=2)[CH2:13][CH2:12]1

参加物

6

反応物 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178525786HCID 178525786、化合物

生成物 1

HCID 178484579(R)-1-(2-(2-Cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)-N,N-dimethylpiperidine-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of dimethylamine (175 μmol) in N,N-dimethylformamide (200 μL) was added triethylamine (35 μL, 250 μmol) and (R)-1-(2-(2-cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (200 μL, 50 μmol, 0.25M in N,N-dimethylformamide) followed by 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate (250 μL, 100 μmol, 0.4M in N,N-dimethylformamide). The reaction mixture was stirred at 50° C. for 16 h. The solvent was removed by Speedvac and the residue was purified via HPLC to afford the title compound. MS API-ES+ (M+H) 392; HPLC retention time 2.43 min (Method C).

後処理

  1. customThe solvent was removed by Speedvac
  2. customthe residue was purified via HPLC

出典と根拠

ORDレコード
ord-2e9914e33760482eae70801b85798f19
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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